You will be picked up from Bari airport and transferred to your accommodation in Matera, one of the oldest settlements in Italy.

The day is yours to explore this fascinating place on foot. Since palaeolithic times man has lived here in dwellings dug into the honey-coloured soft stone of the surrounding hillside. Over centuries more houses were added above and below each other, connected by a maze-like network of stairways and exterior corridors. Looking across the valley, the town looks like a huge human rabbit warren. It’s extremely picturesque and is protected as a world heritage site but not so long ago its inhabitants were amongst the poorest in Italy, living without running water or electricity. You’ll spend a second night in this truly unique town.

Today you are transferred in the afternoon to the town of Alberobello in Puglia. The journey time is just over one hour. Alberobello is a pretty town famous for its many traditional ‘Trulli’ houses. The clever design of these charming, circular stone dwellings keeps the occupants cool during the summer months. The cycling starts tomorrow so the day is yours to enjoy strolling around this charming little town.

Important: As Alberobello has a traffic-free city centre your transfer vehicle will drop you off between 250 and 500 metres from your hotel. You will then proceed to your hotel on foot.

Your first ride leads you through the Valle d’Itria dotted with small hamlets and pretty vineyards. We recommend stopping to taste the wine produced in this region, as it really is very good. Take a break in the pretty, hilltop town of Locorotondo before pressing on eastwards. In the early afternoon you arrive in Ostuni, the ‘white town’, so named because of its whitewashed buildings standing out against the sky. From the top of the town you can enjoy superb views out over the Adriatic coastline 6 kms away to the east. The narrow streets of this quaint little place are a pleasure to explore on foot.

Today’s route leads you south along a network of quiet country lanes to the town of Manduria. You will be riding through a landscape of red earth, olive groves and dry stone walls that typifies Puglia’s charm and appeal. Take a lunch break in the charming old town of Oria clustered around the imposing castle before continuing south to Manduria the capital of the Puglia’s Primitivo grape region.

Today’s quite long but easy ride delivers you to Puglia’s Ionian Coast. We recommend timing your arrival in Porto Cesareo to coincide with lunch as there are some lovely fish restaurants in the pretty little seaside town. A little further along the coast you enjoy a peaceful and scenic ride through the serene Porto Selvaggio nature reserve. You destination today is the fortified port of Gallipoli. The town occupies a strategic position and has a long history of repelling attackers as well as being overrun. A visit to the impressive fortress will provide you with more details on its violent past. The narrow, winding streets of the old town have a Moorish feel to them and are a delight to explore on foot.

Continue south along the Ionian coastline, the route passes numerous idyllic beaches so it’s a good idea to have your swim stuff packed in your pannier today. After this lovely coastal ride you arrive in the small town of Santa Maria di Leuca. The town marks the point where the Ionian and Adriatic seas meet and has that lovely end-of-the-earth, remoteness about it. This is probably why it has attracted quite an eccentric population many of whom live in the numerous, quirky but luxurious villas that abound here. Spend the night in this pleasant little town.

Bid the Ionian Sea farewell and say hello to the Adriatic as you head northwards along its rocky coastline. Today is all about superb sea-views, pretty coastal villages and quaint ports. The swim spots are not as frequent as on yesterday’s ride but they do exist so be sure to pack the swim stuff again. You could also stop off at the Zinzulusa Cave, a stunning Grotto with clear turquoise waters and/or the spa town of Santa Cesarea, known for its sulphurous mineral springs and mud therapy treatments. Otranto itself is an enchanting old town and the waterfront promenade is the perfect place to enjoy a delicious meal after the day’s activities.

Your last day of cycling takes you further along the coast to Torre dell’Orso – a great place for a swim by the way – and then inland to the Baroque city of Lecce. The city has been dubbed the Florence of the South and makes a lovely finale to the cycling holiday. Narrow little streets suddenly open up to reveal baroque treasures seething with detail, like the incredible Basilica di Santa Croce. Historically, Lecce was always the powerhouse of Puglia and this is evident in its opulent and ornate architecture. Perhaps celebrate your achievement with a nice meal in one of the town’s many restaurants.

After breakfast it is time to head for home or your next adventure.